Microbial xylanolytic carbohydrate esterases

Industrial Enzymes: Structure, Function and Applications

Volumn , Issue , 2007, Pages 83-97

  Topakas, Evangelos ^a   Paul, Christakopoulos ^a  

^a NATIONAL TECHNICAL UNIVERSITY OF ATHENS   (Greece)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84892346743     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1007/1-4020-5377-0_6     Document Type: Chapter

References (82)

1. Aliwan, F.O., Kroon, P.A., Faulds, C.B., Pickersgill, R. and Williamson, G. (1999) Ferulic acid esterase- III from Aspergillus niger does not exhibit lipase activity. J. Sci. Food Agric. 79, 457-459.
2. Barbe, C. and Dubourdieu, D. (1998) Characterization and purification of a cinnamate esterase from Aspergillus niger industrial pectinase preparation. J. Sci. Food Agric. 78, 471-478.
3. Biely, P. (1985) Microbial xylanolytic system. Trends Biotechnol. 3, 286-290.
4. Biely, P., MacKenzie, C.R., Puls, J. and Schneider, H. (1986) Cooperativity of esterases and xylanases in the enzymatic degradation of acetyl xylan. Bio Technol. 4, 731-733.
5. Biely, P., MacKenzie, C.R. and Schneider, H. (1988) Production of acetyl xylan esterase by Trichoderma reesei and Schizophyllum commune. Can. J. Microbiol. 34, 767-772.
6. Biely, P., Mastihubova, M., van Zyl, W.H. and Prior, B.A. (2002) Differentiation of feruloyl esterases on synthetic substrates in alpha-arabinofuranosidase-coupled and UV-spectrophotometric assays. Anal. Biochem. 311, 68-75.
7. Biely, P., Wong, K.K.Y., Suckling, I.D. and Spanikova, S. (2003) Transacetylations to carbohydrates catalyzed by acetyl xylan esterase in the presence of organic solvent. Biochem. Biophys. Acta 1623, 62-71.
8. Blum, D.L., Kataeva, I.A., Li, X.L. and Ljungdahl, L.G. (2000) Feruloyl esterase activity of the Clostridium thermocellum cellulosome can be attributed to previously unknown domains of XynY and XynZ. J. Bacteriol. 182, 1346-1351.
9. Borneman, W.S., Ljungdahl, L.G., Hartley, R.D. and Akin, D.E. (1991) Isolation and characterization of p-coumaroyl esterase from the anaerobic fungus Neocallimastix strain MC-2. Appl. Environ. Microbiol. 57, 2337-2344.
10. Borneman, W.S., Ljungdahl, L.G., Hartley, R.D. and Akin, D.E. (1992) Purification and partial characterisation of two feruloyl esterases from the anaerobic fungus Neocallimastix strain MC-2. Appl. Environ. Microbiol. 58, 3762-3766.
11. Castanares, A., McCrae, S.I. and Wood, T.M. (1992) Purification and properties of a feruloyl/p-coumaroyl esterase from the fungus Penicillium pinophilum. Enzyme Microb. Technol. 14, 875-884.
12. Chung, H.-J., Park, S.-M., Kim, H.R., Yang, M.S. and Kim, D.H. (2002) Cloning the gene encoding acetyl xylan esterase from Aspergillus ficuum and its expression in Pichia pastoris. Enzyme Microb. Technol. 31, 384-391.
13. Coutinho, P.M. and Henrissat, B. (1999) Carbohydrate-active enzymes, http:// afmb.cnrs-mrs.fr/CAZY/, server at URL.
14. Crepin, V.F., Faulds, C.B. and Connerton, I.F. (2003a) A non-modular type B feruloyl esterase from Neurospora crassa exhibits concentration-dependent substrate inhibition. Biochem. J. 370, 417-427.
15. Crepin, V.F., Faulds, C.B. and Connerton, I.F. (2003b) Production and characterization of the Talaromyces stipitatus feruloyl esterase FAEC in Pichia pastoris: identification of the nucleophilic serine. Protein Expres. Purif. 29, 176-184.
16. Crepin, V.F., Faulds, C.B. and Connerton, I.F. (2004a) Functional classification of the microbial feruloyl esterases. Appl. Microbiol Biotechnol. 63, 647-652.
17. Crepin, V.F., Faulds, C.B. and Connerton, I.F. (2004b) Identification of a type-D feruloyl esterase from Neurospora crassa. Appl. Microbiol. Biotechnol. 63, 567-570.
18. Dalrymple, B.P., Swadling, Y., Cybinski, D.H. and Xue, G.-P.(1996) Cloning of a gene encoding cinnamoyl ester hydrolase from the ruminal bacterium Butyrivibrio fibrisolvens E14 by a novel method. FEMS Microbiol. Lett. 143, 115-120.
19. Dalrymple, B.P. and Swadling, Y. (1997) Expression of a Butyrivibrio fibrisolvens E14 gene (cinB) encoding an enzyme with cinnamoyl esterase activity is negatively regulated by the product of an adjacent gene (cinR). Microbiology 143, 1203-1210.
20. Dalrymple, B.P., Cybinski, D.H., Layton, I., McSweeney, C.S., Xue, G.-P, Swadling, Y.J. and Lowry J.B. (1997) Three Neocallimastix patriciarum esterases associated with the degradation of complex polysaccharides are members of a new family of hydrolases. Microbiology 143, 2605-2614.
21. Derewenda, Z.S., Derewenda, U. and Dodson, G. (1992) The crystal and molecular structure of the Rhizomucor miehei triacylglyceride lipase at 1.9 A resolution. J. Mol. Biol. 227, 818-839.
22. Donaghy, J. and McKay, A.M. (1997) Purification and characterization of a feruloyl esterase from the fungus Penicillium expansum. J. Appl. Microbiol. 83, 718-726.
23. Donaghy, J.A., Bronnenmeier, K., Soto-Kelly, P.F. and McKay, A.M. (2000) Purification and characterization of an extracellular feruloyl esterase from the thermophilic anaerobe Clostridium stercorarium. J. Appl. Microbiol. 88, 458-466.
24. Dupont, C., Daigneault, N., Shareck, F., Morosoli, R. and Kluepfel, D. (1996) Purification and characterization of an acetyl xylan esterase produced by Streptomyces lividans. Biochem. J. 319, 881-886.
25. Egaña, L., Gutiérrez, R., Caputo, V., Peirano, A., Steiner, J. and Eyzaguirre, J. (1996) Purification and characterization of two acetyl xylan esterases from Penicillium pupurogenum. Biotechnol. Appl. Biochem. 24, 33-39.
26. Faulds, C.B. and Williamson, G. (1991) The purification and characterisation of 4-hydroxy- 3methoxycinnamic (ferulic) acid esterase from Streptomyces olivochromogenes. J. Gen. Microbiol. 137, 2339-2345.
27. Faulds, C.B. and Williamson, G.(1993) Ferulic acid esterase from Aspergillus niger: purification and partial characterization of two forms from a commercial source of pectinase. Biotech. Appl. Biochem. 17, 349-359.
28. Faulds, C.B. and Williamson, G. (1994) Purification and characterization of a ferulic acid esterase (FAE-III) from Aspergillus niger: specificity for the phenolic moiety and binding to microcrystalline cellulose. Microbiology 140, 779-787.
29. Faulds, C.B., Molina, R., Gonzalez, R., Husband, F., Juge, N., Sanz-Aparicio, J. and Hermoso, J.M. (2005) Probing the determinants of substrate specificity of a feruloyl esterase, AnFaeA, from Aspergillus niger. FEBS J. 272, 4362-4371.
30. Ferreira, L.M.A., Wood, T.M., Williamson, G., Faulds, C.B., Hazlewood, G.P. and Gilbert, H.J. (1993) A modular esterase from Pseudomonas fluorescens subsp. cellulosa contains a non-catalytic binding domain. Biochem. J. 294, 349-355.
31. Figueroa-Espinoza, M.-C. and Villeneuve, P. (2005) Phenolic acids enzymatic lipophilization. J. Agric. Food Chem. 53, 2779-2787.
32. Fillingham, I.J., Kroon, P.A., Williamson, G., Gilbert, H.J. and Hazlewood, G.P. (1999) A modular cinnamoyl ester hydrolase from the anaerobic fungus Piromyces equi acts synergistically with xylanase and is part of a multiprotein cellulose-binding cellulose-hemicellulase complex. Biochem. J. 343, 215-224.
33. Fontes, C.M., Hazlewood, G.P., Morag, E., Hall, J., Hirst, B.H. and Gilbert., H.J. (1995) Evidence for a general role for non-catalytic thermostabilizing domains in xylanases from thermophilic bacteria. Biochem. J. 307, 151-158.
34. Garcia-Conesa, M.T., Valerie, F.C., Goldson, A.J., Williamson, G., Cummings, N.J., Connerton, I.F., Faulds, C.B. and Kroon, P.A. (2004) The feruloyl esterase system of Talaromyces stipitatus: production of three discrete feruloyl esterases, including a novel enzyme, TsFaeC, with a broad substrate specificity. J. Biotechnol. 108, 227-241.
35. Ghosh, D., Sawichi, M., Lala, P., Erman, M., Pangborn, W., Eyzaguirre, J., Gutiérrez, R., Jörnvall, H. and Thiel, D.J. (2001) Multiple conformation of catalytic serine and histidine in acetyl xylan esterase at 0.90 A. J. Biol. Chem. 276, 11159-11166.
36. de Graaff, L.H., Visser, J., van den Broeck, H.C., Strozyk, F., Kormelink, F.J.M. and Boonman, J.C.P. (1992) Cloning, expression and use of acetyl xylan esterases from fungal origin. EP 0507369-A 7 07-OCT-1992
37. Hakulinen, N., Tenkanen, M. and Rouvinen, J. (2000) Three-dimensional structure of the catalytic core of acetyl xylan esterase from Trichoderma reesei: insights into the deacetylation mechanism. J. Struct. Biol. 132, 180-190.
38. Halgašová, N., Kutejová, E. and Timko, J. (1994) Purification and some characteristics of the acetyl xylan esterase from Schizophyllum commune. Biochem. J. 298, 751-755.
39. Hall, J., Hazlewood, G.P., Baker, P.J. and Gilbert, H.J. (1988) Conserved reiterated domains in Clostridium thermocellum endoglucanases are not essential for catalytic activity. Gene 69, 29-38.
40. Hermoso, J.A., Sanz-Aparicio, J., Molina, R., Juge, N., Gonzalez, R. and Faulds, C.B. (2004) The crystal structure of feruloyl esterase A from Aspergillus niger suggests evolutive functional convergence in feruloyl esterase family. J. Mol. Biol. 338, 495-506.
41. Juge, N., Williamson, G., Puigserver, A., Cummings, N.J., Connerton, I.F. and Faulds, C.B. (2001) Highlevel production of recombinant Aspergillus niger cinnamoyl esterase (FAEA) in the methylotrophic yeast Pichia pastoris. FEMS Yeast Res. 1, 127-132.
42. Koseki, T., Furuse, S., Iwano, K., Sakai, H. and Matsuzawa, H. (1997) An Aspergillus awamori acetylesterase: purification of the enzyme, and cloning and sequencing of the gene. Biochem. J. 326, 485-490.
43. Koseki, T., Furuse, S., Iwano, K. and Matsuzawa, H. (1998) Purification and characterization of a feruloylesterase from Aspergillus awamori. Biosci. Biotech. Biochem. 62, 2032-2034.
44. Koseki, T., Miwa, Y., Akao, T., Akita, O. and Hashizume, K. (2005a) An Aspergillus oryzae acetyl xylan esterase: Molecular cloning and characteristics of recombinant enzyme expressed in Pichia pastoris J. Biotechnol. in press
45. Koseki, T., Miwa, Y., Fushinobu, S. and Hashizume, K. (2005b) Biochemical characterization of recombinant acetyl xylan esterase from Aspergillus awamori expressed in Pichia pastoris: Mutational analysis of catalytic residues. Biochim. Biophy. Acta 1749, 7-13.
46. Koseki, T., Takahashi, K., Fushinobu, S., Iefuji, H., Iwano, K., Hashizume, K. and Matzuzawa, H. (2005c) Mutational analysis of a feruloyl esterase from Aspergillus awamori involved in substrate discrimination and pH dependence. Biochem. Biophys. Acta 1722, 200-208.
47. Kosugi, A., Murashima, K. and Doi, R.H. (2002) Xylanase and acetyl xylan esterase activities of XynA, a key subunit of the Clostridium cellulovorans cellulosome for xylan degradation. Appl. Environ. Microbiol. 68, 6399-6402.
48. Krastanova, I., Guarnaccia, C., Zahariev, S., Degrassi, G. and Lamba, D. (2005) Heterologous expression, purification, crystallization, X-ray analysis and phasing of the acetyl xylan esterase from Bacillus pumilus. Biochem. Biophys. Acta 1748, 222-230.
49. Kroon, P.A., Faulds, C.B. and Williamson, G. (1996) Purification and characterisation of a novel esterase induced by growth of Aspergillus niger on sugar-beet pulp. Biotechnol. Appl. Biochem. 23, 255-262.
50. Kroon, P.A., Faulds, C.B., Brezillon, C. and Williamson, G. (1997) Methyl phenylalkanoates as substrates to probe the active sites of esterases. Eur. J. Biochem. 248, 245-251.
51. Kroon, P.A., Williamson, G., Fish, N.M., Archer, D.B. and Belshaw, N.J. (2000) A modular esterase from Penicillium funiculosum which releases ferulic acid from plan cell walls and binds crystalline cellulose contains a carbohydrate binding module. Eur. J. Biochem. 267, 6740-6752.
52. Laurie, J.I., Clarke, J.H., Ciruela, A., Faulds, C.B., Williamson, G., Gilbert, H.J., Rixon, J.E., Millward- Sadler, J. and Hazlewood, G.P. (1997) The NodB domain of a multifunctional xylanase from Cellulomonas fimi deacetylates acetyl xylan. FEMS Microbiol. Lett. 148, 261-264.
53. Lawson, D.M., Brzozowski, A.M., Dodson, G.G., Hubbard, R.E., Huge-Jensen, B., Boel, E. and Derewenda, Z.S. (1994) The three-dimensional structures of two lipases from filamentous fungi. In Lipases: Their Biochemistry, Structure and Application (Woolley P and Petersen S, eds), pp. 77-94. Cambridge University Press, Cambridge, UK.
54. Levasseur, A., Pages, S., Fierobe, H.-P., Navarro, D., Punt, P., Belaich, J.-P., Asther, M. and Record, E. (2004) Design and production in Aspergillus niger of a chimeric protein associating a fungal feruloyl esterase and a clostridial dockerin domain. Appl. Environ. Microbiol. 70, 6984-6991.
55. McAuley, K., Svendsen, A., Patkar, S.A. and Wilson, K.S. (2004) Structure of a feruloyl esterase from Aspergillus niger. Acta Cryst. D. 60, 878-887.
56. McCrae, S.I., Leith, K.M., Gordon, A.H. and Wood, T.M. (1994) Xylan degrading enzyme system produced by the fungus Aspergillus awamori: isolation and characterization of a feruloyl esterase and a p-coumaroyl esterase. Enzyme Microb. Technol. 16, 826-834.
57. Millward-Sadler, S.J., Davidson, K., Hazlewood, G.P., Black, G.W., Gilbert, H.J. and Clarke, J.H. (1995) Novel cellulose-binding domains, NodB homologous and conserved modular architecture in xylanases from the aerobic soil bacteria Pseudomonas fluorescens subsp. cellulosa and Cellvibrio mixtus. Biochem. J. 312, 39-48.
58. Nelson, K.E., Clayton, R.A., Gill, S.R., Gwinn, M.L., Dodson, R.J., Haft, D.H. et al. (1999) Evidence for lateral gene transfer between archaea and bacteria from genome sequence of Thermatoga maritima. Nature 399, 323-329.
59. Otto, R.T., Scheib, H., Bornscheuer, U.T., Pleiss, J., Syldatk, C. and Schmid, R.D. (2000) Substrate specificity of lipase B from Candida antarctica in the synthesis of arylaliphatic glycolipids. J. Mol. Catal. B: Enzymatic. 8, 201-211.
60. Page, R., Crzechnik, S.K., Canaves, J.M., Spraggon, G., Kreusch, A., Kuhn, P., Stevens, R.C. and Lesley, S.A. (2003) Shotgun crystallization strategy for structural genomics: an optimized two-tiered crystallization screen against the Thermotoga maritima proteome. Acta Crystallogr. Sect. D Biol. Crystallogr. 59, 1028-1037.
61. Prates, J.A.M., Tarbouriech, N., Charnock, S.J., Fontes, C.M.G.A., Ferreira, L.M.A. and Davies, G.J. (2001) The structure of the feruloyl esterase module of xylanase 10B from Clostridium thermocellum provides insights into substrate recognition. Structure 9, 1183-1190.
62. Record, E., Asther, M., Sigoillot, C., Pages, S., Punt, P.J., Delattre, M., Haon, M., van del Hondel, C.A.M.J.J., Sigoillot, J.-C., Lesage-Meessen, L. and Asther, M. (2003) Overproduction of the Aspergillus niger feruloyl esterase for pulp bleaching application. Appl. Microbiol. Biotechnol. 62, 349-355.
63. Rumbold, K., Biely, P., Mastihubova, M., Gudelj, M., Gubitz, G., Robra, K.-H. and Prior, B.A. (2003) Purification and properties of a feruloyl esterase involved in lignocellulose degradation by Aureobasidium pullulans. Appl. Environ. Microbiol. 69, 5622-5626.
64. Schubot, F.D., Kataeva, I.A., Blum, D.L., Shah, A.K., Ljungdahl, L.G., Rose, J.P. and Wang, B.C. (2001) Structural basis for the substrate specificity of the feruloyl esterase domain of the cellulosomal xylanase Z from Clostridium thermocellum. Biochemistry 40, 12524-12532.
65. Shao, W. and Wiegel, J. (1995) Purification and characterization of two thermostable acetyl xylan esterases from Thermoanaerobacterium sp. strain JW/SL YS485. Appl. Environ. Microbiol. 61, 729-733.
66. Shin, H-D. and Chen, R.R. (2006) Production and characterization of a type B feruloyl esterase from Fusarium proliferatum NRRL 26517. Enzyme Microb. Technol. 38, 478-485.
67. Tarbouriech, N., Prates, J.A.M., Fontes, C.M.G.A. and Davies, G.J. (2005) Molecular determinants of substrate specificity in the feruloyl esterase module of xylanase 10B from Clostridium thermocellum. Acta Cryst. D. 61, 194-197.
68. Tenkanen, M., Schuseil, J., Puls, J. and Poutanen, K. (1991) Production, purification and characterisation of an esterase liberating phenolic acids from lignocellulose. J. Biotechnol. 18, 69-84.
69. Topakas, E., Stamatis, H., Mastihubova, M., Biely, P., Kekos, D., Macris, B.J, and Christakopoulos, P. (2003a) Purification and characterization of a Fusarium oxysporum feruloyl esterase (FoFAE-I) catalysing transesterification of phenolic acid esters. Enzyme Microb. Technol. 33, 729-737.
70. Topakas, E., Stamatis, H., Biely, P., Kekos, D., Macris, B.J. and Christakopoulos, P. (2003b) Purification and characterization of a feruloyl esterase from Fusarium oxysporum catalyzing esterification of phenolic acids in ternary water-organic solvent mixtures. J. Biotech. 102, 33-44.
71. Topakas, E., Stamatis, H., Biely, P. and Christakopoulos, P. (2004) Purification and characterization of a type B feruloyl esterase (StFAE-A) from the thermophilic fungus Sporotrichum thermophile. Appl. Microbiol. Biotechnol. 63, 686-690.
72. Topakas, E., Vafiadi, C., Stamatis, H. and Christakopoulos, P. (2005a) Sporotrichum thermophile type C feruloyl esterase (StFaeC): Purification characterization, and its use for phenolic acid (sugar) ester synthesis. Enzyme Microb. Technol. 36, 729-736.
73. Topakas, E., Christakopoulos, P. and Faulds, C.B. (2005b) Comparison of mesophilic and thermophilic feruloyl esterases: characterization of their substrate specificity for methyl phenylalkanoates. J. Biotechnol. 115, 355-366.
74. Tsujibo, H., Ohtsuki, T., Ito, T., Yamazaki, I., Miyamoto, K., Sugiyama, M. and Inamori, Y. (1997) Cloning and sequence analysis of genes encoding xylanases and acetyl xylan esterase from Stretomyces thermoviolaceus OPC-520. Appl. Environ. Microb. 63, 661-664.
75. Vardakou, M., Flint, J., Christakopoulos, P., Lewis, R.J., Gilbert, H.J. and Murray, J.W. (2005) A family 10 Thermoascus aurantiacus xylanase utilizes arabinose decorations of xylan as significant substrate specificity determinants. J. Mol. Biol. 352, 1060-1067.
76. Vafiadi, C., Topakas, E., Wong, K.K.Y., Suckling, I.D. and Christakopoulos, P. (2005) Mapping the hydrolytic and synthetic selectivity of a type C feruloyl esterase (StFaeC) from Sporotrichum thermophile using alkyl ferulates. Tetrahedron Asymmetry 16, 373-379.
77. Vincent, F., Charnock, S.J., Verschueren, K.H.G., Turkenburg, J.P., Scott, D.J., Offen, W.A., Roberts, S., Pell, G., Gilbert, H.J., Davies, G.J. and Brannigam, J.A. (2003) Multifunctional xylooligosaccharide/ cephalosporin C deacetylase revealed by the hexameric structure of the Bacilus subtilis enzyme at 1.9 A resolution. J. Mol. Biol. 330, 593-606.
78. de Vries, R.P., Michelsen, B., Poulsen, C.H., Kroon, P.A., Heuvel van den, R.H.H., Faulds, C.B., Williamson, G., Hombergh van den, J.P.T.W. and Visser, J. (1997) The faeA genes from Aspergillus niger and Aspergillus tubingensis encode ferulic acid esterases involved in degradation of complex cell wall polysaccharides. Appl. Environ. Microbiol. 63, 4638-4644.
79. de Vries, R.P., vanKuyk, P.A., Kester, H.C.M. and Visser, J. (2002) The Aspergillus niger faeB gene encodes a second feruloyl esterase involved in pectin and xylan degradation and is specifically induced in the presence of aromatic compounds. Biochem. J. 363, 377-386.
80. Wang, X., Geng, X., Egashira, Y. and Sanada, H. (2004) Purification and characterization of a feruloyl esterase from the intestinal bacterium Lactobacillus acidophilus. Appl. Environ. Microbiol. 70, 2367-2372.
81. Williamson, G., Faulds, C.B. and Kroon, P.A. (1998) Specificity of ferulic acid (feruloyl) esterases. Biochem. Soc. Trans. 26, 205-209.
82. Zhang, J.-X., Martin, J. and Flint, H.J. (1994) Identification of non-catalytic conserved regions in xylanases encoded by the xynB and xynD genes of the cellulolytic rumen anaerobe Ruminococcus flavefaciens. Mol. Gen. Genet. 254, 260-264.